What to Do on a First Date

Beauty portrait

Previously, I wrote about how to plan a date and a woman’s mindset on a first date.  Today, I’m revealing all my best tips for the date itself.  With a little bit of practice, you can master first dates.

Here’s how:

  • Greeting her.  How you greet her is up to you – a kiss on the cheek, a slow hug – but two things are not negotiable:  a sly smile and steady eye contact.  This communicates that you’re relaxed, comfortable, friendly and not intimidated.  The opening moments are crucial, and you can get off to a good start immediately.
  • Move slowly.  This sounds strange, but the opening moments of a date are often filled with a quick, nervous energy that feeds on itself.  Walk slowly, relaxed and confident, as you approach her.  Speak slowly.  Show her physically that you’re not nervous (even if you are), and that there’s no reason for her to fear awkwardness.
  • Take the leadership role early.  After you hug her or kiss her cheek, gently (almost imperceptibly) put your hand on her lower back and guide her toward the next location (the seat, the bar, the venue, etc.).  This communicates that you’re the host for tonight and, without being demanding, communicates that she can relax and go along for the ride, free to focus on nothing but the two of you.
  • Sit side by side.  Thanks to your planning of this date, you’ve already chosen a place where you’re sitting side by side or diagonally.  Use this to create incidental touching throughout the date:  fist bumps, ironic high fives, touching her elbow with the back of your hand when you both laugh about something.  These things create a physical intimacy that later will pay off when you kiss her.
  • Have two stories ready for the first conversation.  Her biggest fear is awkwardness, and the biggest awkwardness is that there’s nothing to talk about.  You’re going to eliminate that fear by immediately, upon sitting down together, using your storytelling skills to tell her a personal story for a couple minutes. This is perfect because she can relax, not worry about what to say, and simply study you.  And, because it’s your own personal story, you know that her first impression of you will be a good one.  If the first one doesn’t lead into a conversation, have a second one ready.
  • Avoid standard conversation topics.  When I wrote about banter, I wrote about how important it is to avoid boring, standard topics. On your first date, avoid asking each other (and telling each other) basic facts about your life.  Don’t discuss your job, your family, where you grew up, how many brothers and sisters you each have, etc.  These are things she’s talked about to every guy she’s ever dated. Be different. Be more fun. Use your banter skills and storytelling skills to have a good time.  Even if she asks you what you do for a living, especially at the beginning of the date, you can always playfully redirect the conversation with a smile:  “Let’s talk about something fun and outside of work:  what’s the coolest thing you’ve done this year?”  Most times, she’ll appreciate this, because she didn’t really care about the answer and was just trying to make conversation.
  • Have a handful of stories.  Whenever conversation dies down, tell another personal story.  You’re just guaranteed that the conversation never runs out.
  • Transition to Dating Talk.  Once the conversation feels comfortable – you’ve both told some stories, you’ve both been having fun for a bit and the nervous energy is gone – you’ll want to transition to what I call “Dating Talk”.  Ask her, “What are three qualities you look for in a guy you hang out with?”  This signifies to her that it’s time to talk about dating things.  It changes the mood and (if you’ve done everything right up until now) creates a mood for kissing.
  • Kiss her as a reward.  Women dream of an attractive guy liking them for who they really are.  Give her this experience.  Once you’re into the Dating Talk, wait until she says something that you like (funny, honest, smart, etc.).  Then kiss her as a reward for being awesome.
  • Be confident about the kiss.  Since you’re already sitting side by side and have been touching incidentally, the kiss is not a huge departure.  Simply look her in the eye, look down at her lips, look back in her eyes, and say, “That makes me want to kiss you.”  Assuming she does not suddenly have a horrified look on her face, gently put a finger under her chin to guide her face toward you.  Kiss her lightly – don’t start making out immediately.
  • Break off the kiss. Once you’ve kissed her a bit, stop.  This shows her that you’re not solely interested in physical intimacy.
  • How to know she’s ready to be kissed. My father was a genuine Casanova. He told me the sure fire way to understand if or not to attempt a first kiss, and how to make it work. If and when things are going well…lots of eye contact, smiles, and a relaxed atmosphere…notice when your date’s hands are relaxed and accessible. This will work best if you use your hand farthest away from her, and her hand farthest from you. So when the right opportunity presents itself, gently slip your hand into hers.  If she closes her hand around yours, you’re half way home as she’s just given you the green light. Raise her hand to your lips and kiss the back of her hand while looking her in the eyes. Turn her hand over and kiss the palm while closing your eyes. Then while still holding her hand, gently guide her towards you and kiss her on the lips. If things work out well she’ll be smiling while the maneuver is being conducted, and will remember you for this for a long time to come.
  • Mix it up.  You’re now most of the way home. Spend the rest of the date alternating between fun banter, storytelling, and making out.  Whenever you go too far into one, move to the next.
  • Do not sleep with her.  This might sound strange, but I don’t recommend sleeping with a woman on a first date, even if she’s amenable.  I recommend stopping at making out and resisting anything sexual. It gives you both something to think about for future dates.  In my life I have routinely resisted sex on first dates.
  • Make sure she gets home okay.  Make sure she gets inside her home (if you’re dropping her off), inside a cab (if you’re in a city), or inside her car sober (if she’s driving).  It’s the right thing to do.

With this guide, and a little practice, you should find that almost every date goes smoothly and has a chance for the two of you to connect.

A Woman’s Mindset on a First Date

Womans face and abstract technology.

Recently I wrote about asking women out and about the importance of advance planning for a date.  Before I give you my tips on how to execute flawless dates, it’s important you understand a woman’s mindset on a date.

Here are the most important things to understand:

  • Women are generally looking for you to play host on the date.  Don’t ask her where she wants to go. Don’t let her pick the place. Play host. Design an experience for that evening, and politely guide her through it.  There will be a time, later in your dating relationship, for her to take you on dates and show you what her world looks like.  This isn’t it.
  • Don’t ask her to make any decisions (aside from food and drink orders).  Women have one decision they want to make on a first date:  what they think of you.  Don’t distract her with minor decisions like asking her where in the bar she’d like to sit.  Just decide.  She’ll let you know if there’s something that doesn’t work for her.
  • Her biggest concern is that things will be awkward.  She may or may not be nervous, but she’s definitely concerned that things will be awkward.  It’s awkward if you’re different than your online profile, if the conversation is boring, or if you’re in love with her and she’s not interested.
  • Physical intimacy is an art.  Most women have had experiences where guys have been too physically aggressive on a date.  That can be both scary and disappointing.  But most women have also had experiences where guys don’t make a move at all – leaving them feeling disappointed, unattractive or just confused.
  • She often doesn’t know how long the date is going to last.  She usually plans for multiple scenarios.  If she isn’t attracted to you, she’s going to eject after the first event.  If she is attracted to you, she’ll follow you to a second venue.  In some cases, she may even plan for the possibility of spending a night with you – though this is not a normal assumption for a first date. Before she left home, she probably thought about (and planned for) a couple different outcomes.  If she has roommates, they probably know she may or may not be home early.
  • Her friends are checking in on her.  There are different flavors of this, from “How’s the date going??  Is he hot like his photos?” to the more concerned version of “Is everything okay? I haven’t heard from you.”  You’re not just dating her that night – you’re dating her friends.  She’s likely to text them from the restroom and tell them how the date is going so far.
  • She wants you to kiss her.  Take it from a female:  my friend Nicky once told me, “I wouldn’t go on a date with someone I didn’t want to kiss if things go well.”  Keep this in mind – though the last four words are rather important. Just remember: if the date is going well, you’re letting her down if you don’t kiss her.
  • She’s looking for clues that you’re a gentleman.  She’s looking to see if you hold doors, carry the drinks, speak to the restaurant hostess, and make sure that she gets home safe.  This is something she’ll comment about to her friends.
  • She’s looking for clues that you’re confident and relaxed.  Confident and arrogant is no good – but confident and relaxed shows that you know you belong with someone of her caliber.
  • One thing matters more than the rest.  She wants to have fun.  That’s the single most important thing.  More important than anything you learn about each other. More important than anything you say, do, or feel.  If she has fun with you, it’s the best predictor of a next date.  Anytime you feel things moving too much toward serious questions or conversation, gently steer it back to fun.

Once you understand this mindset from her experience, you’re ready to handle yourself well on the date.  In my next post, I’m bringing you my best tips for how to have a great date.


The Art of Planning a Date

In my last post, I wrote about asking a woman out.  Today, I’d like to talk about actually planning your date.

Good dates are not random events.  Planning a date is a skill that gentlemen master – a skill that can significantly increase the likelihood that you and your date connect.  Here are a few of my tips for planning dates:

  • Think of a date as an event you’re hosting.  You’ll want to plan, think things through, and make sure your guest is comfortable.
  • Choose somewhere that gives a glimpse into your life:  since women are always interpreting, choose a place that says something about you.  Choose a bar you enjoy, a bookstore you love, an activity that is your hobby.  Make sure your date planning says something about you and that it’s something attractive.  It’s better to show her who you are than to plan something fancy that doesn’t resemble your everyday life.
  • Take her somewhere she’s never been before. If you take her to the same place other men have taken her, you’re already appearing to be like every other guy she’s dated.  This means that, in your spare time, you should find a handful of spots that women you date probably haven’t been to.
  • Set a very clear and easy meeting place.
  • Have a nearby place to hang out while you wait for her to arrive.  You should be ready for your date to be late – and you don’t want to be waiting there for her. Instead, tell her you’ll be nearby and that she should text you when she arrives. Hang out at a nearby place where you can kill time.  Then, when she texts, you will be at a conveniently close location and can walk or drive over in a few minutes; this shows that you have your own life you’re living and, if she’s late, she’s not going to see you as the guy who’s been waiting there for 15 minutes with nothing better to do.
  • Plan three locations over the course of the night.  Psychology studies report that people feel much closer when they’ve been to multiple locations together.  How long you spend at each is not as important.  You could start with an art gallery (free, plenty to discuss, can be done in 20 minutes), then go for a drink, and then switch locations for a nightcap. By the end of the night, it almost feels like three dates.
  • Choose places that allow you to sit side-by-side or diagonal.  Don’t take a date somewhere you must sit across the table from her. It makes it difficult to touch her playfully and practically impossible to kiss her. Find venues that have couches where you can sit comfortably side by side.
  • Your locations should be arranged chronologically to increase intimacy.  Don’t start at a dark candlelit bar sitting next to each other and then transition to a bright public space with lots of people around.  The idea of a date is to sink into each other.  As you’ll see in the next post on the date itself, you’ll want to make sure that the last location is conducive to the two of you kissing discretely.
  • Last, think of what the woman will need to wear.  If you’re taking her somewhere fancy where she may be wearing heels, don’t then plan something where she needs to walk around a museum in uncomfortable shoes.  Women think about this.  You should too.

With these basics, you should be able to plan a three-venue date that increases intimacy, gets you talking and touching, and leads to the kind of date you’ll both want more of.

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